If you have any doubts about her sanity, this photo should confirm them. Her eyes are totally dead. She is either drugged to the gills or she has some very, very serious problems. If they let her out in less than 22 days, they are making a serious mistake. They should take a photo of her the day she is released and compare them. Her expression is scary beyond belief. Jail will not make the demons go away. Years of therapy and living a clean and sober life will do that. I’m not holding my breath. This photo is sad on many levels.

Lindsay's Officially Behind Bars! What Do You Think Of Her Booking Photo? I Think She Looks Good!

July 19, 2010: Dina Lohan arrives home at midnight after returning from dinner and drinks at BLVD Restaurant, just eight hours before her daughter Lindsay Lohan is scheduled to turn herself in to jail at the Beverly Hills Court in Beverly Hills., CAalifornia. (INFphoto.com_

Lindsay Lohan’s July 2007 Booking Photo.

Steve-O

Mischa Barton

Matthew McConaughey

Macaulay Culkin

Lil Kim

Kimora Lee Simmons

Haley Joel Osment

Charlie Sheen

Chace Crawford

Andy Dick

Amy Winehouse

Al Gore III

Lindsay Lohan

Dina Lohan goes on a fast food run in Hollywood, stopping first at In ‘N’ Out Burger and then at Wendy’s before heading back to her daughter Lindsay Lohan’s West Hollywood apartment with the bags of food and drinks. 7/12/10

Dina Lohan goes on a fast food run in Hollywood, stopping first at In ‘N’ Out Burger and then at Wendy’s before heading back to her daughter Lindsay Lohan’s West Hollywood apartment with the bags of food and drinks. 7/12/10

Considering she’s heading to jail for potentially 90 days, I think she looks as good as she does on some of her latest magazine covers.

Remember this date, July 20, as the day Lindsay Lohan went to jail… again. Lindsay, 24, officially checked into Century Regional Detention Facility in Lynwood, Calif., and she’s in for a seriously rude awakening. As HollywoodLife.com already told you, Lindsay will have to spend most of her day confined in her jail cell without her cell phone, her cigarettes or even her precious Twitter!

But all things considered, I think she actually managed to take a pretty good booking photo. She’s wearing just the right amount of eyeliner, not too much lipstick, and she even got her roots touched up! It’s a good thing, too, because this photo is going to be pulled out time and time again in the future. It’s better to leave the public with a positive image than be haunted by some of the ugly mugshots in our above gallery.